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Educator advocates have important roles in the pursuit of educational equity for transgender students. In this paper, we explore one educator advocate’s experiences navigating a district administrator’s personal discomfort with transgender inclusion, which he deployed in situations when he believed her proposals for gender-inclusive policies and practices were “running wild” and too far away from the institutional status quo. This case study addresses the limitations of individualistic approaches to transgender student inclusion and lends insight to how educator advocates navigate tensions between transgender stigma and their professional obligations to secure safety and provide optimal learning environments for all students.